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D-A-A type C<^>N ligand compound as well as C<^>N ring platinum complex and application thereof

A D-A-A, ligand compound technology, applied in the field of organic electroluminescence, can solve the problems of constraints, few types of infrared electroluminescent materials, and easy quenching of luminescence

Active Publication Date: 2013-10-09
XIANGTAN UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

At present, the main problems of near-infrared electroluminescent materials and electroluminescent devices of cyclometal platinum complexes are: (1) There are few varieties of near-infrared electroluminescent materials of organic cyclometal platinum complexes, and the range of options is narrow , it is difficult to meet the needs of high-efficiency near-infrared electroluminescent devices; (2) common organic ring metal platinum complex near-infrared electroluminescent materials are easy to crystallize, and the luminescence is easy to quench under high current density; (3) Near-infrared organic / polymer electroluminescent devices constructed of cyclometal platinum complex near-infrared electroluminescent materials generally have low luminous efficiency, luminous brightness and service life. Practical applications of electroluminescent materials and their organic / polymer electroluminescent devices in the fields of optical fiber communication, infrared light source and infrared pump laser

Method used

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  • D-A-A type C&lt;^&gt;N ligand compound as well as C&lt;^&gt;N ring platinum complex and application thereof
  • D-A-A type C&lt;^&gt;N ligand compound as well as C&lt;^&gt;N ring platinum complex and application thereof
  • D-A-A type C&lt;^&gt;N ligand compound as well as C&lt;^&gt;N ring platinum complex and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] n-C 8 h 17 Synthesis of OTPA-BT-Q Ligand

[0061] 1.1 Synthesis of 4-n-octoxy iodobenzene

[0062] In a 250mL single-necked bottle, add 20.00g (90.91mmol) p-iodophenol, 26.34g (136.48mmol) n-octane bromide, 25.10g (180.58mmol) anhydrous potassium carbonate, 100mL acetone, and reflux for 24h under nitrogen protection. The reaction was stopped, and after cooling to room temperature, the reaction solution was poured into 150 mL of distilled water, extracted with dichloromethane (3×30 mL), and the organic layer was washed with anhydrous MgSO 4 dry. Filtration, rotary distillation under reduced pressure to remove the solvent, the obtained crude product was separated by 200-300 mesh silica gel column chromatography with petroleum ether as eluent to obtain 27.80 g of colorless transparent liquid with a yield of 92.1%. 1 H NMR (400MHz, CDCl 3 ,ppm):7.54(d,J=8.6Hz,2H),6.68(d,J=8.6Hz,2H),3.94-3.96(t,J=6.5Hz,2H),1.81-1.79(t,J= 4.2Hz,2H),1.46-1.16(m,10H),0.90-0.87(t,J=7.4Hz,3...

Embodiment 2

[0075] i-C 8 h 17 Synthesis of Cz-BT-Q Ligand

[0076] 2.1 Synthesis of 4-bromo-7-(9-isooctylcarbazol-2-yl)-2,1,3-benzothiadiazole

[0077] In a 100mL single-necked bottle, add 1.60g (3.95mmol) 2-(9-isooctyl) carbazole borate, 1.38g (4.74mmol) 4,7-dibromo-2,1,3-benzo Thiadiazole, 8 mL of 2M potassium carbonate aqueous solution, 8 mL of anhydrous methanol, 137 mg (0.12 mmol) of tetrakis(triphenylphosphine) palladium, 40 mL of toluene, reacted at 80° C. for 12 h under nitrogen protection. Stop the reaction, after cooling to room temperature, the reaction solution was poured into 150mL distilled water, extracted with dichloromethane (3 × 30mL), the organic layer was anhydrous MgSO 4 dry. Filtration, the solvent was distilled off under reduced pressure, and the residue was separated by 200-300 mesh silica gel column chromatography with dichloromethane:petroleum ether=1:5 (V / V) as the eluent to obtain 1.18g of a yellow viscous substance , and the yield was 61.2%. 1 H NMR (400...

Embodiment 3

[0083] 3.1 n-C 8 h 17 The synthesis of OTPA-BT-QPtpic complex, the structural formula is as follows:

[0084]

[0085] In a 50mL single-necked bottle, add 150mg (0.20mmol) n-C 8 h 17 OTPA-BT-Q ligand, 65 mg (0.16 mmol) potassium chloroplatinite (K 2 PtCl 4 ), 5 mL of distilled water and 15 mL of ethylene glycol monoethyl ether were reacted at 80° C. for 24 h under nitrogen protection. Cool to normal temperature, add 25mL distilled water, extract the mixture with dichloromethane (3×15mL), combine the organic phase with anhydrous MgSO 4 Dry, distill off the solvent under reduced pressure, and dry in a vacuum oven to obtain 140 mg of a purple-black solid, which is the chlorine bridged product (n-C 8 h 17 OTPA-BT-Q) 2 (μ-Cl) 2 Pt(II), with a yield of 90.7%, was directly used in the next step of de-bridging reaction.

[0086] In a 50mL single-necked bottle, add 140mg (0.07mmol) (n-C 8 h 17 OTPA-BT-Q) 2 (μ-Cl) 2 Pt(II), 34mg (0.28mmol) picolinic acid, 30mg (0.28mmol...

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Abstract

The invention discloses a D-A-A type C<^>N ligand compound as well as a C<^>N ring platinum complex and an application thereof. The D-A-A type C<^>N ligand compound is synthesized for the first time, and a D-A-A type C<^>N ring platinum complex is further synthesized on such a basis; when the D-A-A type C<^>N ring platinum complex is used as an electroluminescence materials to be applied to preparation of polymer near-infrared electroluminescence devices, the prepared near-infrared electroluminescence devices are high in light emitting efficiency and high in light emitting strength; by using the compound, the option range of near-infrared electroluminescence materials is widened.

Description

technical field [0001] The present invention relates to a D-A-A type C Λ N ligand compound and its C Λ The invention relates to an N-ring metal platinum complex and its application, belonging to the field of organic electroluminescence. technical background [0002] With the popularization of today's network technology and digital multimedia technology, information light source, as an indispensable part of large-capacity and high-speed optical communication, optical storage and photoelectric display technology, is playing an increasingly important role, and has aroused the attention of many scientists. Great interest. [0003] At present, information light sources are mainly composed of inorganic materials (such as III and V compounds) and semiconductor light-emitting devices. However, the manufacturing process of inorganic semiconductor light-emitting devices is very complicated, the equipment is expensive, and the purity of materials is very high. In order to reduce pro...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D417/14C07D401/04C07F15/00C09K11/06H01L51/54
Inventor 朱卫国于俊婷谭华王亚飞刘煜朱美香
Owner XIANGTAN UNIV
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